This just popped up on Ask.MetaFilter: How do you tell a friend that their dreams aren't realistic?

I know it's not GROOVY to be a PARTY POOPER and tell someone not to pursue their dreams. I usually tell people to do so and to work hard at it and I really mean it. But in THIS CASE, for a certain friend, I just can't get myself to do it! ...

I can very much relate to this feeling. I've been on both sides.

First, keep this principle in mind: If you have dreams and passions and don't pursue them, you will always regret it. So, knowing that, it's better for your friend to fail--and fail hard--pursuing his dreams, rather than have the kind of regret that pops up later in mid-life crises.

Second, try to give charitable criticism. Instead of telling your friend your perspective, try to walk with him through the process of thinking. Don't ask him questions that are leading, like, "So, did you make a plan yet? hmmm?" Instead try to think of questions that you would ask if you were his fan. "So what are you up to next?" You know, actually be curious.

Be open to a 50-50 chance that he could reveal something about where he's going that you just didn't have any idea about.

That's what it means to be charitable. And charitable friends are ones everybody should have. And through the process of talking it out and having a soundboard, there's theoretically a 50% chance he'll see the error of his ways anyway, and reform. But more often than not, if done right, you'll maybe help him refine his goals a little and your opinion of him will change a lot.